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$87+ Cheap flights from Indiana to Winnipeg (YWG)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 11/2. Fares are subject to change and may not be available on all flights or dates of travel.
IND — YWG
Oct 16 — Oct 231
Thu 10/16
Thu 10/23
1 adult, Economy
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Cheap flight deals from Indiana to Winnipeg

Keep the following information in mind while searching for Indiana to Winnipeg flight deals. Data was last updated September 16, 2025.

Round-trip from

$208
(Kiwi.com)

One-way from

$87
(Trip.com)
From Indiana to Winnipeg
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One-way flight from Indiana to Winnipeg
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Find flight deals from Indiana to Winnipeg

Cheapest flights from Indiana to Winnipeg
Explore the most affordable flight options available from Indiana to Winnipeg. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 16, 2025.

This Kiwi.com deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/65:30 pmORD - YWG
1 stop15h 31mWestJet
Sun 10/128:30 amYWG - ORD
1 stop8h 13mWestJet
Deal found 9/14$208
This Vliegwinkel deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Vliegwinkel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/95:30 pmORD - YWG
1 stop29h 40mWestJet
Sun 10/128:30 amYWG - ORD
1 stop8h 13mWestJet
Deal found 9/15$211
This Kiwi.com deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/65:30 pmORD - YWG
2 stops17h 56mWestJet
Fri 10/178:30 amYWG - ORD
1 stop8h 13mWestJet
Deal found 9/14$214
This Kiwi.com deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/105:30 pmORD - YWG
1 stop18h 11mWestJet
Sun 10/128:30 amYWG - ORD
1 stop8h 13mWestJet
Deal found 9/15$215
This Kiwi.com deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/306:20 amMDW - YWG
2 stops18h 21mMultiple Airlines
Fri 10/317:30 amYWG - MDW
1 stop11h 09mMultiple Airlines
Deal found 9/15$216
This Kiwi.com deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/115:30 pmORD - YWG
2 stops17h 56mWestJet
Fri 10/178:30 amYWG - ORD
1 stop8h 13mWestJet
Deal found 9/14$216
This Kiwi.com deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/125:30 pmORD - YWG
1 stop15h 31mWestJet
Fri 10/178:30 amYWG - ORD
1 stop8h 13mWestJet
Deal found 9/14$218
This Kiwi.com deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/65:30 pmORD - YWG
2 stops17h 56mMultiple Airlines
Mon 10/139:00 amYWG - ORD
1 stop14h 44mMultiple Airlines
Deal found 9/14$233
This Kiwi.com deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/83:12 pmORD - YWG
1 stop25h 10mMultiple Airlines
Mon 10/139:00 amYWG - ORD
1 stop14h 44mMultiple Airlines
Deal found 9/14$234
This Kiwi.com deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/65:30 pmORD - YWG
1 stop15h 31mWestJet
Thu 10/169:05 pmYWG - ORD
1 stop19h 38mWestJet
Deal found 9/14$235
This Kiwi.com deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/115:30 pmORD - YWG
2 stops17h 56mMultiple Airlines
Mon 10/139:00 amYWG - ORD
1 stop14h 44mMultiple Airlines
Deal found 9/14$236
This Kiwi.com deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/95:05 amORD - YWG
1 stop11h 17mMultiple Airlines
Fri 10/178:30 amYWG - ORD
1 stop8h 13mMultiple Airlines
Deal found 9/14$238

Cheapflights Fare Finder

 
Customize your flight search to find flights from Indiana to Winnipeg that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated September 16, 2025.
Use the filters below to find and compare flights from Indiana to Winnipeg that are best for you.

Fly from

Indiana

Fly to

Winnipeg

Route

Depart

Return

Price

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Thu 10/30

6:20 am-12:41 am

2 stops18h 21m

Winnipeg

Fri 10/31

7:30 am-6:39 pm

1 stop11h 09m

$216

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Fri 10/10

5:30 pm-11:41 am

1 stop18h 11m

Winnipeg

Wed 10/15

9:05 pm-4:43 pm

1 stop19h 38m

$241

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Thu 10/16

5:30 pm-2:30 pm

1 stop21h 00m

Winnipeg

Fri 10/24

9:05 pm-4:43 pm

1 stop19h 38m

$259

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Mon 10/6

5:30 pm-9:01 am

1 stop15h 31m

Winnipeg

Thu 10/16

9:00 am-11:39 pm

1 stop14h 39m

$273

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Fri 9/26

5:30 pm-6:15 pm

1 stop24h 45m

Winnipeg

Mon 9/29

9:00 am-5:26 pm

1 stop8h 26m

$294

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Sun 10/26

2:20 pm-10:08 am

1 stop19h 48m

Winnipeg

Wed 11/5

7:50 am-6:25 am

3 stops22h 35m

$330

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Fri 10/31

2:20 pm-10:41 pm

1 stop8h 21m

Winnipeg

Wed 11/5

7:30 am-6:49 pm

1 stop11h 19m

$332

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Thu 10/9

9:26 pm-4:22 pm

1 stop18h 56m

Winnipeg

Sun 10/12

8:10 pm-8:39 am

1 stop12h 29m

$340

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Wed 10/29

7:20 am-12:43 am

2 stops17h 23m

Winnipeg

Fri 10/31

7:30 am-4:56 pm

1 stop9h 26m

$340

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Thu 10/9

5:30 pm-11:10 pm

1 stop29h 40m

Winnipeg

Sun 10/12

6:30 am-6:14 pm

2 stops11h 44m

$358

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/15

Showing 1-10 of 44 results
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Best time to book a flight from Indiana to Winnipeg

Have a flexible travel schedule? Discover the best time to fly to Winnipeg from Indiana with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Indiana to Winnipeg

What is the cheapest time of day to fly from IN to YWG?

Find hourly flight availability from Indiana to Winnipeg. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 16, 2025.

When flying from Indiana to Winnipeg, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Related info for your journey

Find useful and relevant information for your journey from Indiana to Winnipeg. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly into for flights to Winnipeg from Indiana?

    Winnipeg (YWG) is the airport you will fly into if you book a flight from Indiana to Winnipeg. It is only a 4.6 mi journey from Winnipeg (YWG) to Winnipeg’s city center.

  • How long is the flight from Indiana to Winnipeg?

    A quick flight from Indiana to Winnipeg can take about 14h. WestJet provides one of the quickest options available for as low as $517. The distance from Indiana to Winnipeg is about 936 mi. This flight may include one or multiple stops.

  • What are the most popular routes from Indiana to Winnipeg?

    When deciding which route to take from Indiana to Winnipeg consider Chicago O'Hare Intl - Winnipeg, Chicago Midway - Winnipeg or Cincinnati Cinci./N. Kentucky - Winnipeg as they are the most popular.

  • Can I find deals for flights from Indiana to Winnipeg that include hotel bookings?

    Yes. In addition to deals on Indiana to Winnipeg flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Indiana to Winnipeg?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Indiana to Winnipeg.

  • Can I find deals for business class flights from Indiana to Winnipeg?

    Yes. Cheapflights offers flight deals from Indiana to Winnipeg by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Indiana to Winnipeg?

    Currently, August is the cheapest month in which you can book a flight from Indiana to Winnipeg (average of $358). Flying from Indiana to Winnipeg in December is currently the most expensive (average of $501). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Winnipeg?

Book flights to Winnipeg if you plan to visit one of these locations
Portage la Prairie

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Alternative routes for Indiana to Winnipeg

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Top airline flying from Indiana to Winnipeg

Discover the top airline that operate flights from Indiana to Winnipeg. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated September 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$400Average$794FlexibilityNo cancel feeOn-timeN/A

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